Acetyl chloride → HCID 66877264, compound

HRID 1863976Notes

Reaction equation

HRID 1863976 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[CH2:5]([O:12][C:13]([N:15]1[CH2:20][C@H:19]([O:21][CH2:22][C:23]2[CH:24]=[CH:25][C:26]3[O:31][CH2:30][CH2:29][N:28]([CH2:32][CH2:33][CH2:34][O:35][CH3:36])[C:27]=3[CH:37]=2)[C@@H:18]([C:38]2[CH:43]=[CH:42][C:41]([CH2:44][O:45][CH2:46][C@@H:47]([CH3:51])[CH2:48][O:49][CH3:50])=[CH:40][CH:39]=2)[C@H:17]([CH2:52][NH2:53])[CH2:16]1)=[O:14])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(N(CC)CC)C>ClCCl>[CH2:5]([O:12][C:13]([N:15]1[CH2:20][C@H:19]([O:21][CH2:22][C:23]2[CH:24]=[CH:25][C:26]3[O:31][CH2:30][CH2:29][N:28]([CH2:32][CH2:33][CH2:34][O:35][CH3:36])[C:27]=3[CH:37]=2)[C@@H:18]([C:38]2[CH:43]=[CH:42][C:41]([CH2:44][O:45][CH2:46][C@@H:47]([CH3:51])[CH2:48][O:49][CH3:50])=[CH:40][CH:39]=2)[C@H:17]([CH2:52][NH:53][C:1](=[O:3])[CH3:2])[CH2:16]1)=[O:14])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 66877137HCID 66877137, compound

Product 1

HCID 66877264HCID 66877264, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5.936 mmol of acetyl chloride are added to a solution of 5.396 mmol of (3R,4R,5R)-3-aminomethyl-4-[4-((S)-3-methoxy-2-methyl-propoxymethyl)-phenyl]-5-[4-(3-methoxy -propyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-piperidine-1-carboxylic acid benzyl ester and 6.475 mmol of triethylamine in 80 ml of dichloromethane under argon at 0° C. After 30 minutes, the reaction mixture is quenched with saturated aqueous sodium bicarbonate solution and extracted with tert-butyl methyl ether (2×). The combined organic layers are washed successively with water and brine, dried with sodium sulfate and evaporated. The residue is purified by flash chromatography (SiO2 60F) to afford the title compound as a yellow oil. Rt=4.98 (gradient I).

Workup

  1. customthe reaction mixture is quenched with saturated aqueous sodium bicarbonate solution
  2. extractionextracted with tert-butyl methyl ether (2×)
  3. washThe combined organic layers are washed successively with water and brine
  4. dry with materialdried with sodium sulfate
  5. customevaporated
  6. customThe residue is purified by flash chromatography (SiO2 60F)

Sources & evidence

ORD record
ord-cbfb866baab34c64b45865cbf8746008
Source dataset
uspto-grants-2009_12
Patent number
US07625893B2

Reaction notes

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